HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Islip

$71+ Cheap flights from Chicago (CHI) to Islip, NY (ISP)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ISP
févr. 11 — févr. 181
mer. 2/11
mer. 2/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Islip with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Islip

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Islip (ISP). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated janvier 12, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$151
(CheapOair)

One-way from

$71
(CheapOair)

Popular in

June

Cheapest in

January

Average price

$149
Provider with most accurate pricing for Chicago (CHI)-Islip Long Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Islip Long Island flights.
Search Deals
From Chicago (CHI) to Islip Long Island
Search Deals
One-way flight from Chicago (CHI) to Islip Long Island
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Find flight deals from Chicago to Islip

Cheapest flights from Chicago to Islip
Explore the most affordable flight options available from Chicago to Islip. Find the lowest fares from popular airlines and budget airlines, with prices last updated on janvier 12, 2026.

This CheapOair deal was found by Cheapflights users on 1/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 2/2612:15 pm
ORD
-
ISP
1 stop26h 57m
Frontier
sam. 3/1410:43 am
ISP
-
ORD
1 stop14h 01m
Frontier
Deal found 1/11$151
This CheapOair deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 1/293:55 pm
ORD
-
ISP
1 stop25h 43m
Frontier
dim. 2/19:25 am
ISP
-
ORD
1 stop26h 16m
Frontier
Deal found 1/12$171
This CheapOair deal was found by Cheapflights users on 1/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/314:18 pm
ORD
-
ISP
1 stop25h 53m
Frontier
dim. 4/126:00 am
ISP
-
ORD
1 stop18h 03m
Frontier
Deal found 1/11$191
This CheapOair deal was found by Cheapflights users on 1/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 4/210:12 am
ORD
-
ISP
1 stop7h 59m
Frontier
lun. 4/68:19 pm
ISP
-
ORD
1 stop13h 43m
Frontier
Deal found 1/11$221
This CheapOair deal was found by Cheapflights users on 1/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 3/184:18 pm
ORD
-
ISP
1 stop22h 31m
Frontier
ven. 3/2010:43 am
ISP
-
ORD
1 stop9h 46m
Frontier
Deal found 1/11$236
This CheapOair deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 1/158:08 pm
ORD
-
ISP
1 stop22h 42m
Frontier
jeu. 1/227:43 pm
ISP
-
ORD
1 stop15h 52m
Frontier
Deal found 1/12$252
This CheapOair deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 2/2612:15 pm
ORD
-
ISP
1 stop26h 57m
Frontier
dim. 3/15:07 pm
ISP
-
ORD
1 stop29h 27m
Frontier
Deal found 1/12$257
This CheapOair deal was found by Cheapflights users on 1/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 3/511:55 am
ORD
-
ISP
1 stop23h 52m
Frontier
dim. 3/85:08 pm
ISP
-
ORD
1 stop23h 20m
Frontier
Deal found 1/11$260
This Kiwi.com deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 1/2710:07 am
ORD
-
ISP
2 stops24h 03m
Multiple Airlines
sam. 1/317:35 pm
ISP
-
ORD
1 stop15h 08m
Multiple Airlines
Deal found 1/12$270
This CheapOair deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 1/3011:45 am
ORD
-
ISP
1 stop8h 02m
Frontier
dim. 2/19:25 am
ISP
-
ORD
1 stop26h 16m
Frontier
Deal found 1/12$271
This CheapOair deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 1/293:55 pm
ORD
-
ISP
1 stop25h 43m
Frontier
jeu. 2/57:43 pm
ISP
-
ORD
1 stop15h 52m
Frontier
Deal found 1/12$283
This CheapOair deal was found by Cheapflights users on 1/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 1/2311:45 am
ORD
-
ISP
1 stop8h 02m
Frontier
dim. 1/259:25 am
ISP
-
ORD
1 stop26h 16m
Frontier
Deal found 1/11$286

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Islip that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated janvier 12, 2026.
Use the filters below to find and compare flights from Chicago to Islip that are best for you.

Fly from

Chicago

Fly to

Islip

Route

Depart

Return

Price

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

mar. 3/31

4:18 pm-7:11 pm

1 stop25h 53m

Islip Long Island

dim. 4/12

6:00 am-11:03 pm

1 stop18h 03m

$191

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

jeu. 4/2

10:12 am-7:11 pm

1 stop7h 59m

Islip Long Island

lun. 4/6

8:19 pm-9:02 am

1 stop13h 43m

$220

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

jeu. 1/22

3:55 pm-6:38 pm

1 stop25h 43m

Islip Long Island

ven. 1/30

7:33 pm-4:35 pm

1 stop22h 02m

$237

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

sam. 2/7

7:00 am-6:55 pm

1 stop10h 55m

Islip Long Island

dim. 2/8

7:53 pm-4:58 pm

1 stop22h 05m

$252

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

jeu. 3/5

11:55 am-12:47 pm

1 stop23h 52m

Islip Long Island

dim. 3/8

5:08 pm-3:28 pm

1 stop23h 20m

$260

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

jeu. 3/19

8:05 am-3:49 pm

1 stop6h 44m

Islip Long Island

jeu. 3/26

5:08 pm-11:38 pm

1 stop7h 30m

$261

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

mar. 1/27

10:07 am-11:10 am

2 stops24h 03m

Islip Long Island

sam. 1/31

7:35 pm-9:43 am

1 stop15h 08m

$270

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

ven. 1/23

11:45 am-8:47 pm

1 stop8h 02m

Islip Long Island

dim. 1/25

9:25 am-10:41 am

1 stop26h 16m

$286

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

mar. 2/24

8:30 am-8:40 am

1 stop23h 10m

Islip Long Island

sam. 2/28

5:07 pm-9:34 pm

1 stop29h 27m

$296

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

mar. 2/10

8:30 am-1:13 pm

1 stop27h 43m

$71

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/12

Showing 1-10 of 18 results
1
2

Compare providers for flights from Chicago to Islip

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Islip in January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Islip, New York flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Islip, New York flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Islip, New York flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Islip, New York flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Islip, New York flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Islip

Have a flexible travel schedule? Discover the best time to fly to Islip from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Islip

What is the cheapest month to book a flight from Chicago to Islip, New York?

Currently, January is the cheapest month in which you can book a flight from Chicago to Islip, New York (average of $35). Flying from Chicago to Islip, New York in July is currently the most expensive (average of $104). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Islip

Get insights into the airlines that provide service to Islip. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Islip. Reviews last updated janvier 12, 2026.
Read through reviews of airlines operating flights from Chicago to Islip, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,256 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Chicago to Islip. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Islip from Chicago?

    Most people fly into Islip Long Island (ISP) if they book a flight to Islip from Chicago. On average, Long Island has 0 inbound flights from Chicago per day from 0 airlines. Islip Long Island is conveniently located just 7.2 mi from Islip’s city center.

  • How long is the flight from Chicago to Islip, New York?

    There are many flights that can get you from Chicago to Islip, New York in 25h 53m. Fly via Frontier to get the fastest option. There are 770 mi between Chicago and Islip, New York.

  • Can I find deals for flights from Chicago to Islip that include hotel bookings?

    Yes. In addition to deals on Chicago to Islip flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Islip?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Islip.

  • Can I find deals for business class flights from Chicago to Islip?

    Yes. Cheapflights offers flight deals from Chicago to Islip by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Islip, New York?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Islip, New York (average of $35). Flying from Chicago to Islip, New York in July is currently the most expensive (average of $104). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Islip?

Book flights to Islip if you plan to visit one of these locations
Riverhead

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Islip

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
Midway to John F Kennedy Intl flights
Midway to Newark flights
St. Louis to LaGuardia flights
Midway to LaGuardia flights
St. Louis to Newark flights
St. Louis to John F Kennedy Intl flights
O'Hare Intl to Buffalo flights
O'Hare Intl to Syracuse flights
O'Hare Intl to Albany flights
O'Hare Intl to Rochester flights
O'Hare Intl to White Plains flights
Midway to Syracuse flights
Moline to LaGuardia flights
Midway to Buffalo flights
Peoria to LaGuardia flights
Moline to Newark flights
Midway to Albany flights
Peoria to Newark flights
Moline to John F Kennedy Intl flights
O'Hare Intl to Islip flights
St. Louis to Buffalo flights
Bloomington to John F Kennedy Intl flights
Peoria to John F Kennedy Intl flights
Midway to White Plains flights
Midway to Rochester flights
St. Louis to Albany flights
Bloomington to Newark flights
Bloomington to LaGuardia flights
O'Hare Intl to Rutland flights
St. Louis to Rochester flights
O'Hare Intl to Ithaca flights
St. Louis to Syracuse flights
St. Louis to White Plains flights
Bloomington to White Plains flights
Moline to Syracuse flights
St. Louis to Ithaca flights
Champaign to LaGuardia flights
Champaign to John F Kennedy Intl flights
Midway to Ithaca flights
Evansville to Newark flights
Evansville to John F Kennedy Intl flights
Moline to Rochester flights
Champaign to Newark flights
O'Hare Intl to Watertown flights
Peoria to Rochester flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.